3-Hydroxybutyric Acid → Dodecyl 3-Hydroxybutyrate
Reaction equation
[OH:1][CH:2]([CH3:7])[CH2:3][C:4]([OH:6])=[O:5].[CH2:8](O)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].S(=O)(=O)(O)O>>[OH:1][CH:2]([CH3:7])[CH2:3][C:4]([O:6][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH3:8])=[O:5]Participants
4
Conditions
- Temperature
- 120 °C
Procedure
A 500 mL one neck round bottom flask equipped with a Dean Stark trap, condenser, and a nitrogen inlet/outlet was charged with 72.0 g (69 mmole) of 3-hydroxybutyric acid, 268.5 g (1.45 mole) of dodecyl alcohol, and 0.36 g of sulfuric acid. The mixture was heated to 120° C. for 48 hours and water was collected as the reaction proceeded. The acid was neutralized by washing three times with 100 mL saturated NaHCO3 solution. The organic layer was collected and dried over MgSO4 and concentrated. Excess dodecanol was removed by high vacuum distillation to yield 117.65% (60% yield) of clear oil (91% pure by GC).